₩220,900 Cheap Flights from Boston (BOS) to Chicago (MDW)

View ₩220,900 flight on Sun, Oct 5, 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago Midway Airport (MDW)

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Cheap Flights from Boston to Chicago (BOS-MDW)

Prices were available within the past 7 days and start at ₩220,900 for one-way flights and ₩430,400 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Oct 30 - Mon, Nov 3
BOS
Boston
MDW
Chicago
₩430,400 Roundtrip, found 6 days ago
₩430,400
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Oct 30 from Boston to Chicago, returning Mon, Nov 3, priced at ₩430,400 found 6 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩453,700 Roundtrip, found 5 days ago
₩453,700
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩453,700 found 5 days ago
Delta
Thu, Oct 30 - Mon, Nov 3
BOS
Boston
MDW
Chicago
₩499,700 Roundtrip, found 6 days ago
₩499,700
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Oct 30 from Boston to Chicago, returning Mon, Nov 3, priced at ₩499,700 found 6 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩523,200 Roundtrip, found 5 days ago
₩523,200
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩523,200 found 5 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩550,900 Roundtrip, found 5 days ago
₩550,900
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩550,900 found 5 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩564,800 Roundtrip, found 5 days ago
₩564,800
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩564,800 found 5 days ago
Delta
Thu, Oct 30 - Mon, Nov 3
BOS
Boston
MDW
Chicago
₩569,200 Roundtrip, found 6 days ago
₩569,200
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Oct 30 from Boston to Chicago, returning Mon, Nov 3, priced at ₩569,200 found 6 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩592,500 Roundtrip, found 5 days ago
₩592,500
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩592,500 found 5 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩620,200 Roundtrip, found 5 days ago
₩620,200
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩620,200 found 5 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
MDW
Chicago
₩634,200 Roundtrip, found 5 days ago
₩634,200
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩634,200 found 5 days ago

Find the cheapest month to fly from Boston (BOS) to Chicago (MDW)

September is typically the cheapest month to fly

From ₩105,544 - ₩461,256 per traveler.

Frequently asked questions

How much is a flight from Logan Intl. Airport to Midway Intl. Airport (MDW)?
Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from Logan Intl. Airport (BOS) to MDW start from ₩430,400. Make your booking today to score the best price for your journey. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to MDW?
The majority of flights can be canceled online, but whether you are charged a fee depends on your airline. If you do need to cancel your getaway, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for BOS to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Logan Intl. Airport (BOS) to Chicago Airport?
You can forget about a movie marathon on this flight — it's only 1,400 kilometers from Boston to Chicago. Find your seat, get comfortable and you'll be there before you know it.
Which airlines fly direct from Logan Intl. Airport to Chicago Airport?
If you're looking to fly directly from Logan Intl. Airport to MDW, Southwest Airlines (WN) is an excellent choice. It operates 121 flights every month between Boston and Chicago.
Are Logan Intl. Airport (BOS) to MDW flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes pick up a bargain, with some super cheap airfares from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) showing up a few weeks prior to the departure date. If you'd rather plan ahead, Expedia compares and updates all the best flight deals continually — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines advertise prices that far in advance.

Travel information

Travel information

Origin airport
Logan Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
₩430,400
Distance
1371 km
Average flight time
1 hour 37 mins

Book with confidence

Book with confidence

Boston to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Boston to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with BOS to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Boston for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Boston to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Boston to O'Hare Intl.
₩176,700
*Available to Expedia members.